Sodium hydride → diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate

HRID 1748269ノート

反応式

HRID 1748269 の反応式
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:22][CH:23]1OS(=O)(=O)[N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][CH2:24]1.[NH4+].[Cl-]>CN(C=O)C>[C:34]([O:33][C:31]([NH:26][CH2:25][CH2:24][CH:23]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:22])=[O:32])([CH3:37])([CH3:36])[CH3:35]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2 回HCID 86682388Tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide

生成物 1

HCID 67236468diethyl 1-{4-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-indole-2,6-dicarboxylate収率 133.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

To a stirred suspension of 60% NaH dispersion in mineral oil (78.8 mg, 2.0 mmol) in DMF (2.5 mL) cooled to 0° C. is added a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 561 mg, 2.1 mmol) in DMF (3 mL). The mixture is stirred for 20 min and a solution of tert-butyl 6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide (450 mg, 1.8 mmol) in DMF (2.5 mL) is added. The reaction mixture is stirred for 30 min at 0° C. and it is warmed to room temperature and stirred for 48 h. Saturated NH4Cl solution is added and the reaction mixture is extracted with EtOAc. The organic layer is separated, washed with water, then brine, dried (MgSO4) and concentrated to afford the title compound (1.04 g, 50% pure) as an oil.

後処理

  1. stirringThe reaction mixture is stirred for 30 min at 0° C.
  2. temperatureit is warmed to room temperature
  3. stirringstirred for 48 h
  4. extractionthe reaction mixture is extracted with EtOAc
  5. customThe organic layer is separated
  6. washwashed with water
  7. dry with materialbrine, dried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-8c12f7bfa7754c81b77bf51e26af72f3
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

読み込み中…